6-nitroindoline
6-nitroindole
Conditions | Yield |
---|---|
With oxygen; salcomine In methanol at 25℃; for 5h; | 92% |
With manganese(IV) oxide In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; | 92% |
With isolated cobalt single atom sites stabilized on an ordered porous nitrogen doped carbon matrix In 1,3,5-trimethyl-benzene at 120℃; for 8h; Schlenk technique; | 92% |
6-nitroindole
Conditions | Yield |
---|---|
In ethylene glycol at 170℃; Retro Diels-Alder reaction; Inert atmosphere; | 92% |
2-ethynyl-5-nitroaniline
6-nitroindole
Conditions | Yield |
---|---|
With [cyclopentadienylruthenium(II) bis-(2-diphenylphosphino-6-t-butylpyridine)(acetonitrile)]hexafluorophosphate In tetrahydrofuran-d8 at 70℃; for 2h; Sealed tube; | 92% |
Conditions | Yield |
---|---|
With sodium tungstate; dihydrogen peroxide In methanol; water at 20℃; for 7h; | A 7% B 79% |
6-nitroindole
Conditions | Yield |
---|---|
With Amberlyst 15 In 2-methyltetrahydrofuran at 100℃; for 0.75h; Microwave irradiation; | 70% |
Conditions | Yield |
---|---|
In methanol; N,N-dimethyl-formamide for 0.0833333h; Heating; | A 57% B 22% C 6% |
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide for 1h; Heating; | A 54% B 13% |
2,4-dinitrotoluene
N,N-dimethyl-formamide dimethyl acetal
6-nitroindole
Conditions | Yield |
---|---|
Stage #1: 2,4-dinitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 5h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere; Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis; | 52% |
diethyl malonate
1-methoxy-6-nitroindole
A
6-nitroindole
B
diethyl 2-(6-nitroindol-3-yl)methylmalonate
Conditions | Yield |
---|---|
With potassium hydride In N,N-dimethyl-formamide for 0.0833333h; Heating; | A 20% B 40% C 5% |
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide for 1h; Heating; | A 4% B 15% |
6-Nitro-1H-indole-2-carboxylic Acid
6-nitroindole
Conditions | Yield |
---|---|
With quinoline; copper(II) oxide |
6-nitro-1H-indole-3-carboxylic acid
6-nitroindole
Conditions | Yield |
---|---|
With quinoline at 180℃; |
N-chloromethylsulfonyl-6-nitroindoline
6-nitroindole
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h; |
acetaldehyde-(3-nitro-phenylhydrazone)
A
6-nitroindole
B
4-nitro-1H-indoIe
Conditions | Yield |
---|---|
GIPKh-115 In acetonitrile at 200 - 320℃; (g) phase; | |
GIPKh-115 In acetonitrile at 180 - 320℃; (g) phase. Object of study: effect of electronic factors; |
1-hydroxy-6-introindole
6-nitroindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / methanol / 20 °C 2: 4 percent / dimethylformamide; H2O / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 96 percent / methanol / 20 °C 2: 57 percent / dimethylformamide; methanol / 0.08 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 96 percent / methanol / 20 °C 2: 20 percent / KH (35 percent in mineral oil) / dimethylformamide / 0.08 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid / <5 2: maleic acid-anhydride; palladium; water View Scheme | |
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid / <5 2: tetrachloro-<1,4>benzoquinone; xylene View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 0 - 20 °C 2: manganese(IV) oxide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 0 - 20 °C 2: manganese(IV) oxide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; HNO3 2: aqueous KOH 3: quinoline / 180 °C View Scheme |
6-nitro-1H-indole-2-carboxylic acid ethyl ester
6-nitroindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH 2: copper (II)-oxide; quinoline View Scheme |
6-nitro-indole-3-carboxylic acid ethyl ester
6-nitroindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous KOH 2: quinoline / 180 °C View Scheme |
ethyl 2-[2-(3-nitrophenyl)hydrazinylidene]propanoate
6-nitroindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: polyphosphoric acid 2: aq.-ethanolic KOH 3: copper (II)-oxide; quinoline View Scheme |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate under 2587.7 Torr; | 100% |
100% | |
With silver tetrafluoroborate; 4,4'-Dimethoxy-2,2'-bipyridin; potassium tert-butylate; hydrogen In 1,4-dioxane at 80℃; under 30003 Torr; for 48h; Autoclave; | 94% |
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0℃; | 100% |
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 98% |
6-nitroindole
p-toluenesulfonyl chloride
N-[4-(methylphenyl)sulfonyl]-6-nitro-1H-indole
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 99% |
6-nitroindole
(2-trimethylethylsilylethoxy)methyl chloride
6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃; for 16h; Inert atmosphere; | 98.7% |
Stage #1: 6-nitroindole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 0℃; for 10h; | 38% |
6-nitroindole
t-butyl 4-bromomethyl-3-methoxybenzoate
tert-butyl 3-methoxy-4-<(6-nitroindol-1-yl)methyl>benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 48h; Heating; | 98% |
6-nitroindole
1-chloro 4-iodobutane
1-(4-chlorobutyl)-6-nitro-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.0833333h; Stage #2: 1-chloro 4-iodobutane In N,N-dimethyl-formamide at 20℃; for 0.5h; | 97.6% |
With sodium hydride In N,N-dimethyl-formamide |
6-nitroindole
ethyl bromoacetate
(6-nitro-indol-1-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide for 0.416667h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 26h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36h; | 88% |
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 0 - 25℃; Product distribution / selectivity; | 57% |
6-nitroindole
1-methyl-6-nitro-indole
Conditions | Yield |
---|---|
With CH3I; NaH In dimethylformamide [DMF]; water | 97% |
With potassium carbonate; methyl iodide In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 126℃; for 2h; Concentration; Reflux; Green chemistry; | 96% |
With potassium carbonate In n-heptane; water; ethyl acetate; N,N-dimethyl-formamide | 96.1% |
6-nitroindole
trifluoroacetic anhydride
2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole; trifluoroacetic anhydride In N,N-dimethyl-formamide at 60℃; for 3h; Stage #2: With water; sodium hydrogencarbonate In ethyl acetate; N,N-dimethyl-formamide | 96% |
In tetrahydrofuran at 0 - 25℃; for 18h; | 40% |
6-nitroindole
benzenesulfonyl chloride
6-nitro-1-(phenylsulfonyl)-1H-indole
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 0 - 20℃; for 24h; | 96% |
Stage #1: 6-nitroindole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; | 77% |
6-nitroindole
methyl 4-(bromomethyl)-3-methoxybenzoate
methyl 3-methoxy-4-<(6-nitroindol-1-yl)methyl>benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 48h; Heating; | 95% |
With potassium carbonate In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux; | 38% |
With potassium carbonate In dichloromethane; ethyl acetate; acetone |
Conditions | Yield |
---|---|
With copper(l) iodide; metformin hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 95% |
Conditions | Yield |
---|---|
With 4,4'-sulfonediphenol In acetic acid butyl ester at 80℃; for 2h; Friedel-Crafts Alkylation; Sealed tube; Green chemistry; | 95% |
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h; Stage #2: ethyl bromide With sodium iodide In N,N-dimethyl-formamide; mineral oil | 94.5% |
6-nitroindole
1-bromomethyl-3,5-difluoro-benzene
1-(3,5-difluoro-benzyl)-6-nitro-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.25h; Stage #2: 1-bromomethyl-3,5-difluoro-benzene In DMF (N,N-dimethyl-formamide) | 94% |
Stage #1: 6-nitroindole With 1-methyl-pyrrolidin-2-one; cesium carbonate at 0℃; for 0.5h; Stage #2: 1-bromomethyl-3,5-difluoro-benzene at 20℃; for 18h; | |
Stage #1: 6-nitroindole With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #2: 1-bromomethyl-3,5-difluoro-benzene In DMF (N,N-dimethyl-formamide) for 1h; |
Conditions | Yield |
---|---|
In water at 80℃; for 24h; Friedel-Crafts reaction; | 93% |
cyclopropyl trifluoromethyl ketone
6-nitroindole
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 8h; | 93% |
Conditions | Yield |
---|---|
With aluminium(III) chloride hexahydrate; sodium dodecyl-sulfate; silica gel In neat (no solvent) at 20℃; for 0.5h; Milling; Green chemistry; | 93% |
6-nitroindole
Conditions | Yield |
---|---|
In 2,2,2-trifluoroethanol at 40℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; | 93% |
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II) In water at 120℃; for 16h; Sealed tube; | 92% |
Conditions | Yield |
---|---|
With Pf0A9 E104G enzyme In aq. phosphate buffer; water; dimethyl sulfoxide at 75℃; for 12h; pH=8; Reagent/catalyst; Enzymatic reaction; | 91% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; oxygen; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 80℃; for 12h; regioselective reaction; | 91% |
6-nitroindole
4-bromomethyl-3-methoxybenzonitrile
1-(4-cyano-2-methoxybenzyl)-6-nitroindole
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 90% |
6-nitroindole
1-iodo-3-chloro-propane
1-(3-chloropropyl)-6-nitro-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide at 20℃; for 3h; | 90% |
With sodium hydride In N,N-dimethyl-formamide |
The IUPAC name of 6-Nitroindole is 6-nitro-1H-indole. With the CAS registry number 4769-96-4, it is also named as 1H-Indole, 6-nitro-. The product's categories are Blocks; Indoles Oxindoles; Nitro Compounds; Indoles and Derivatives; Pharmacetical; Indole Derivative; Indoles; Simple Indoles. Besides, it is yellow to brown-yellow powder, which should be stored in sealed, dark, ventilated and dry place at room temperature. In addition, its molecular formula is C8H6N2O2 and molecular weight is 162.15.
The other characteristics of this product can be summarized as: (1)EINECS: 225-311-0; (2)ACD/LogP: 1.87; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.87; (5)ACD/LogD (pH 7.4): 1.87; (6)ACD/BCF (pH 5.5): 15.6; (7)ACD/BCF (pH 7.4): 15.6; (8)ACD/KOC (pH 5.5): 248.67; (9)ACD/KOC (pH 7.4): 248.67; (10)#H bond acceptors: 4; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.723; (14)Molar Refractivity: 45.07 cm3; (15)Molar Volume: 113.7 cm3; (16)Surface Tension: 67.7 dyne/cm; (17)Density: 1.425 g/cm3; (18)Flash Point: 173.1 °C; (19)Melting Point: 137-143 °C; (20)Enthalpy of Vaporization: 58.46 kJ/mol; (21)Boiling Point: 362.6 °C at 760 mmHg; (22)Vapour Pressure: 3.98E-05 mmHg at 25 °C.
Preparation of 6-Nitroindole: this chemical can be prepared by 6-Nitro-indoline.
This reaction needs O2, Bis(salicylidene)ethylenediaminatoCo(II) and Methanol at temperature of 25 °C. The reaction time is 5 hours. The yield is 92 %.
Uses of 6-Nitroindole: this chemical is used as organic reagent and pharmaceutical intermediate. Moreover, it can be used to produce Indol-6-ylamine.
This reaction needs H2, 10 percent Pd/C and Ethyl acηte. The yield is 100 %.
When you are using this chemical, please be cautious about it as the following: it is possible risk of irreversible effects. You should wear suitable protective clothing and gloves. In case of accident or if you feel unwell, please seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)SMILES: c1cc(cc2c1cc[nH]2)[N+](=O)[O-]
(2)InChI: InChI=1/C8H6N2O2/c11-10(12)7-2-1-6-3-4-9-8(6)5-7/h1-5,9H
(3)InChIKey: PSWCIARYGITEOY-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C8H6N2O2/c11-10(12)7-2-1-6-3-4-9-8(6)5-7/h1-5,9H
(5)Std. InChIKey: PSWCIARYGITEOY-UHFFFAOYSA-N
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